Structure-activity relationships among substituted N-benzoyl derivatives of phenylalanine and its analogs in a microbial antitumor prescreen I: Derivatives of o-fluoro-DL-phenylalanine.
Twelve derivatives of 0-fluoro-dl-phenylalanine containing fluorine, chlorine, methoxy, and nitro radicals in various positions of the aromatic ring of the benzoyl group were prepared and tested in a Lactobacillus casei system. It was found that most substitutions in the benzoyl phenyl ring resulted in a compound exhibiting greater growth-inhibiting activity than the nonsubstituted benzoyl-o-fluorophenylalanine. The greatest activity was observed in the ortho-substituted fluoro compound and the meta- and para-substituted chloro and nitro compounds. With the methoxy group, the position of substitution appeared unimportant, since all three methoxy isomers exhibited essentially equal inhibition. Nitro substitution in the ortho position had a protective effect in that the product was less active than the unsubstituted benzoyl-o-fluoro-dl-phenylalanine.
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001419:Bacteria / Q000187:drug effects*; D055598:Chemical Phenomena; D002621:Chemistry; D007780:Lacticaseibacillus casei / Q000187:drug effects; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; C027217:2-fluorophenylalanine; D010649:Phenylalanine